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Piperonylic acid

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Piperonylic acid Basic information
Product Name:Piperonylic acid
Synonyms:1,3-BENZODIOXOLE-5-CARBOXYLIC ACID;3,4-METHYLENDIOXYBENZOIC ACID;3,4-(METHYLENEDIOXY)BENZOIC ACID;RARECHEM AL BO 0210;3,4-(methylenedioxy)benzoic acid, piperonylic acid;Piperonylic acid, 98+%;PIPEROYLICACID;3,4-Methylendioxybenzoic acid 98%
CAS:94-53-1
MF:C8H6O4
MW:166.13
EINECS:202-342-8
Product Categories:Building Blocks;C8;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Benzodiozoles, Benzodioxines & Benzodioxepines;Carboxylic Acids;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzodiozoles, Benzodioxines & Benzodioxepines;Carboxylic Acids;Quinoxalines ,Quinazolines ,Quinaldines
Mol File:94-53-1.mol
Piperonylic acid Structure
Piperonylic acid Chemical Properties
Melting point 229-231 °C (lit.)
Boiling point 254.32°C (rough estimate)
density 1.3579 (rough estimate)
refractive index 1.5090 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility DMSO (Slightly), Methanol (Slightly)
pka4.35±0.20(Predicted)
form Powder
color Off-white to beige
Water Solubility slightly soluble
Merck 14,7477
BRN 150206
Cosmetics Ingredients FunctionsSKIN PROTECTING
SKIN CONDITIONING
InChI1S/C8H6O4/c9-8(10)5-1-2-6-7(3-5)12-4-11-6/h1-3H,4H2,(H,9,10)
InChIKeyVDVJGIYXDVPQLP-UHFFFAOYSA-N
SMILESOC(=O)c1ccc2OCOc2c1
LogP0.810 (est)
CAS DataBase Reference94-53-1(CAS DataBase Reference)
NIST Chemistry Reference1,3-Benzodioxole-5-carboxylic acid(94-53-1)
EPA Substance Registry System1,3-Benzodioxole-5-carboxylic acid (94-53-1)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-37/38-41-36/37/38
Safety Statements 26-36/37/39-37/39
WGK Germany 3
RTECS DF4912765
Hazard Note Irritant
TSCA TSCA listed
HS Code 29329970
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
Piperonylic acid English
ACROS English
SigmaAldrich English
ALFA English
Piperonylic acid Usage And Synthesis
Chemical PropertiesIt is a white to light yellow crystalline powder, slightly soluble in water, chloroform, cold ethanol, and ether.
UsesPiperonylic Acid is a compound closely mimicking the structure of transcinnamic acid involved in the phenylpropanoid pathway in plant physiology.
DefinitionChEBI: Piperonylic acid is a member of the class of benzodioxoles that is 1,3-benzodioxole substituted by a carboxy group at position 5. It is a natural product isolated from several plant species. It is a selective mechanism-based inactivator of the trans-cinnamate 4-hydroxylase enzyme and exhibits antifungal and skin wound healing properties. It has a role as a plant metabolite, an EC 1.14.14.91 ( trans-cinnamate 4-monooxygenase) inhibitor, a vulnerary and an antifungal agent. It is a member of benzodioxoles, a monocarboxylic acid and an aromatic carboxylic acid. It is a conjugate acid of a piperonylate.
Synthesis Reference(s)The Journal of Organic Chemistry, 40, p. 3803, 1975 DOI: 10.1021/jo00913a051
Purification MethodsCrystallise the acid from EtOH or water. [Beilstein 19/7 V 300.]
References[1] OTTO RICHARD GOTTLIEB MAURO T M. Isolation of Piperonylic Acid from Ocotea pretiosa[J]. Nature, 1958, 182 4637: 742-743. DOI:10.1038/182742b0.
[2] SEUNG HYUN HAN. Piperonylic Acid Promotes Hair Growth by Activation of EGFR and Wnt/β-Catenin Pathway.[J]. International Journal of Molecular Sciences, 2024, 25 19. DOI:10.3390/ijms251910774.
[3] SCHALK. Piperonylic acid, a selective, mechanism-based inactivator of the trans-cinnamate 4-hydroxylase: A new tool to control the flux of metabolites in the phenylpropanoid pathway[J]. Plant Physiology, 1998, 118 1: 209-218. DOI:10.1104/pp.118.1.209.
Tag:Piperonylic acid(94-53-1) Related Product Information
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